EP3378883A1 - Thermoplastische zusammensetzungen und entsprechende verarbeitungsmethoden und artikel - Google Patents

Thermoplastische zusammensetzungen und entsprechende verarbeitungsmethoden und artikel Download PDF

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Publication number
EP3378883A1
EP3378883A1 EP17162039.6A EP17162039A EP3378883A1 EP 3378883 A1 EP3378883 A1 EP 3378883A1 EP 17162039 A EP17162039 A EP 17162039A EP 3378883 A1 EP3378883 A1 EP 3378883A1
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Prior art keywords
composite
group
polymer
represented
ppa
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EP17162039.6A
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English (en)
French (fr)
Inventor
Joel Flores
Glenn P. Desio
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Solvay Specialty Polymers USA LLC
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Solvay Specialty Polymers USA LLC
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Priority to EP17162039.6A priority Critical patent/EP3378883A1/de
Publication of EP3378883A1 publication Critical patent/EP3378883A1/de
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    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2377/06—Polyamides derived from polyamines and polycarboxylic acids

Definitions

  • the invention relates to thermoplastic composites including a polymer matrix, having a polyphthalamide polymer, and continuous reinforcing fibers.
  • the invention further relates to the fabrication of thermoplastic composites.
  • the invention still further relates articles incorporating the thermoplastic composites.
  • thermoplastic composites are gaining a significant amount of attention as a potential replacement for metal parts. Relative to metal parts, thermoplastic composites can provide a significant reduction in weight and cost, while simultaneously providing desirable or superior mechanical performance.
  • One type of polymer used in thermoplastic composites is amorphous polypthalamide ("PPA") polymers.
  • PPA polypthalamide
  • the popularity of amorphous PPA polymers in thermoplastic composites is at least in part due to the fact that they form crack-free composites.
  • thermoplastic composites are being investigated for use in a wider variety of application settings, which require greater mechanical performance (e.g. tensile strength) and chemical performance (e.g. chemical resistance). In general, for many of these applications settings, amorphous PPA polymers are not able to meet the increased mechanical performance and chemical performance requirements of these new application settings.
  • thermoplastic composites including a polymer matrix, having a at least one semi-crystalline polyphthalamide (“PPA”) polymer, and at least one continuous reinforcing fiber.
  • PPA semi-crystalline polyphthalamide
  • incorporation of semi-crystalline PPA polymers, having a selected melt profile, into the polymer matrix provided for crack-free thermoplastic composites.
  • fabrication of thermoplastic composites from semi-crystalline PPA polymers results in composites having significant visible cracking, which compromises the mechanical integrity of the composite and makes in undesirable for use in many application settings.
  • crack-free thermoplastic composites having a semi-crystalline polymer matrix can be formed from semi-crystalline PPA polymers having a selected inherent viscosity, crystallinity and difference between onset degradation temperature and the melting temperature.
  • the thermoplastic composite can have improved tensile strength, chemical resistance and thermal stability, relative to composites incorporating an amorphous PPA polymer.
  • the composites can be formed using melt impregnation techniques, well known in the art.
  • the composites can be desirably used in a wide range of application settings including, but not limited to automotive, aerospace, oil and gas and mobile electronic device applications.
  • the polymer matrix includes at least one semi-crystalline PPA polymer and, optionally, at least one additive. It was surprisingly found that semi-crystalline PPA polymers having a selected processing profile provided for crack free thermoplastic composite.
  • the melt profile refers to a combination of properties of the semi-crystalline PPA polymer. The properties are the inherent viscosity (" ⁇ inh "), the crystallinity, and the thermal window. As described in detail below, the crystallinity of the PPA polymers is measured according to the heat of fusion (“ ⁇ H f ").
  • the thermal window refers to the difference in the onset degradation temperature ("Td”) and the melting temperature (“Tm”) of the PPA polymer, as represented by the following formula : T d - T m .
  • the thermoplastic composite includes at least 20 wt.%, at least 25 wt.%, at least 30 wt.%, at least 35 wt.% or at least 40 wt.% of the polymer matrix, relative to the total weight of the composite. Additionally or alternatively, the thermoplastic composite includes no more than 80 wt.%, no more than 70 wt.%, no more than 60 wt.%, no more than 55 wt.%, no more than 50 wt.% or no more than 45 wt.% of the polymer matrix, relative to the total weight of the composite.
  • the polymer matrix includes at least one semi-crystalline PPA polymer.
  • a semi-crystalline PPA polymer is a PPA polymer having a heat of fusion that is at least 3 joules per gram ("J/g").
  • a PPA polymer refers to any polymer including recurring unit (R PA ) and recurring unit (R* PA ), where the total concentration of recurring unit (R PA ) and recurring unit (R* PA ) is at least 50 mole percent ("mol%"), relative to the total number of moles of recurring units in the polymer.
  • the total concentration of recurring unit (R PA ) and recurring unit (R* PA ) in the PPA polymer is at least 60 mol%, at least 70 mol%, at least 80 mol%, at least 90 mol%, at least 99 mol% or at least 99.5 mol% recurring unit (R PA ), relative to the total number of moles of recurring units in the PPA polymer.
  • Recurring unit (R PA ) is represented by the following formula : [-M A -M B -] (1) where -M A - and -M B - are represented by the following formulae, respecitvely : and and where R 1 and R 2 , at each instance, is independently selected from the group consisting of a halogen, an alkyl, an alkenyl, an ether, a thioether, an ester, an amide, an imide, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, an alkali or alkaline earth metal phosphonate, an alkyl phosphonate, an amine, and an quaternary ammonium; i, at each instance, is an integer from 0 to 2; j is an integer from 0 to 4; and n is 4, 6 or 10.
  • a dashed bond represents a bond to an atom outside the drawn structure.
  • the carbon atom in each -(CR 1 i )- has 2 - i hydrogen atoms bonded to it.
  • the central benzene ring has 4 - j ring carbons bonded to a hydrogen atom.
  • j 1, 3 of the benzyl carbons are bonded to a hydrogen and one is bonded to R 2 . Analogous notation is used for the other formulae herein.
  • Recurring unit (R* PA ) is represented by either one of following formulae : [-M* A -M* B -], (4) and where -M* A - is represented by a formula selected from the following group of formulae : and and -M* B - is represented by a formula selected from the following group of formulae :
  • the R 1* , R 2* and R 3 to R 8 is independently selected from the group consisting of a halogen, an alkyl, an alkenyl, an ether, a thioether, an ester, an amide, an imide, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, an alkali or alkaline earth metal phosphonate, an alkyl phosphonate, an amine, and an quaternary ammonium; i*, k and s, at each instance, are independently selected integers from 0 to 2; L is an integer from 5 to 12; n* is 5 to 7, preferably 4, 6 or 10; t is an integer from 6 to 18; m, p and r are independently selected integers from 0 to 8; and j* and q are independently selected integers from 0 to 4.
  • each i and j are zero; each i*, j*, k, m, p, q, r and s are zero; or each i, j, i*, j*, k, m, p, q, r and s are zero.
  • -M A - and -M B - are respectively referred to as a diamine diradical and a dicarboxylic acid diradical.
  • H-M A -H and HO-M B -OH are a diamine and a dicarboxylic acid monomer, respectively, and that polycondensation of H-M A -H with HO-M B -OH results in formation of the recurring unit (R PA ) (amide bond between -M A - and -M B - and the loss of water).
  • reference to -M A - as a diamine diradical refers to the radical formed by the deprotonation of the terminal -H atoms in the formula H-M A -H.
  • reference to -M B - as a dicarboxylic acid diradical refers to the radical formed by the dehydroxylation of the terminal -OH groups in the formula HO-M B -OH.
  • reference to -M A - as a 1,6-hexamethylenediamine diradical refers to Formula (3), where each i is zero and n is 6.
  • reference to -M B - as a terephthalic acid diradical refers to Formula (3), where j is zero.
  • groups according to Formula (5) are referred to as amino acid diradicals.
  • the person of ordinary skill in the art will recognize that HO---CO-(CR 3 k ) L -NH---H is an amino acid, and that polycondensation of the aminoacid results in formation of the recurring unit (R* PA ) (dehyroxylation and dehydrogenation of the terminal HO--- and ---H, respectively, and the formation of water).
  • R* PA recurring unit
  • groups according to Formula(5) can be formed by polycondensation of caprolactams.
  • R* PA recurring unit
  • recurring unit (R* PA ) is represented by Formula (4)
  • -M A - and -M*A - are the same
  • -M* A - is represented by Formula (6)
  • -M* B - is represented a formula selected from the group of formulae consisting of Formula (13) to (15).
  • the concentration of recurring unit (R* PA ) is from 30 mol% to 50 mol%, relative to the total concentration of recurring units (R PA ) and (R* PA ).
  • -M* B - is represented by Formula (15).
  • -M* B - is a diradical of a dicarboxylic acid selected from the group consisting of adipic acid; heptanedioic acid; octanedioic acid; 1,3-cyclohexanedicarboxylic acid and 1,4-cyclohexanedicarboxylic acid and -M B - is a terephthalic acid diradical.
  • -M A - and -M* A - are a diradical of a diamine selected from the group consisting 1,4-butanediamine; 1,6-hexamethylenediamine; and 1,10-decanediamine.
  • -M* A - is represented by a formula selected from the group consisting of Formulae (6) to (11), preferably the group consisting of Formulae (8) to (11), and -M* B - is represented by Formula (12).
  • the concentration of recurring unit (R* PA ) is from 5 to 40 mol%, relative to the total concentration of recurring units (R PA ) and (R* PA ).
  • -M* A - is a diamine diradical selected from the group consisting of 1,5-diaminopentane; 2-methyl-1,5-diaminopentane; 3-methyl-1,6-hexamethylenediamine; 2,5-dimethyl-1,6-hexamethylenediamine; 2,2,4-trimethyl-1,6-hexamethylenediamine; 2,4,4-trimethyl-1,6-hexamethylenediamine; 1,7-diaminoheptane; 1,3-bis(aminomethyl)cyclohexane ("1,3-BAC”); 1,4-bis(aminomethyl)cyclohexane ("1,4-BAC”); bis(4-aminocyclohexyl)methane (“BACM”); bis(4-amino-3-methylcyclohexyl)methane (“MACM”); 5-amino-1,3,3-trimethylcyclohexanemethylamine (“IPDA”); m-x
  • -M B - and -M* B - are terephthalic acid diradicals.
  • -M A - is a diradical of a diamine selected from the group consisting 1,4-butanediamine; 1,6-hexamethylenediamine; and 1,10-decanediamine.
  • recurring unit (R* PA ) is represented by Formula (5).
  • recurring unit (R* PA ) is a diradical of an amino acid or lactam selected from the group consisting of 5-aminopentanoic acid, 6-aminohexanoic acid, 7-aminoheptanoic acid; and 11-aminoundecanoic acid.
  • -M B - is a terephthalic acid diradical.
  • -M A - is a diradical of a diamine selected from the group consisting 1,4-butanediamine; 1,6-hexamethylenediamine; and 1,10-decanediamine.
  • the at least one semi-crystalline PPA polymer can include additional recurring units, distinct from recurring unit (R PA ) and recurring unit (R* PA ).
  • the total concentration of recurring unit (R PA ), recurring unit (R* PA ) and other distinct recurring units represented by a formula according to Formula (1) is at least 50 mol%, at least 60 mol%, at least 70 mol%, at least 80 mol%, at least 90 mol%, at least 99 mol% or at least 99.5 mol%, relative to the total number of moles of recurring units in the polymer.
  • the at least one semi-crystalline PPA polymer includes from 50 mol% to 95 mol% of recurring unit (R PA ) and from 5 mol% to 50 mol% of recurring unit (R* PA ), relative to the total number of moles of recurring units in the PPA polymer.
  • crack-free composites can be formed from a polymer matrix incorporating a semi-crystalline PPA polymer with specifically selected melt profile.
  • the semi-crystalline PPA polymers of interest herein have an inherent viscosity of at least 0.8 deciliters per gram ("dL/g").
  • the at least one semi-crystalline PPA polymer has an inherent viscosity of at least 0.9 dL/g or at least 1.0 dL/g.
  • the PPA polymers can have an inherent viscosity of no more 1.6 dL/g, 1.5 dL/g or 1.4 dL/g. The inherent viscosity can be measured as described in the Examples below.
  • the crystallinity of the PPA polymers can be determined by measuring the heat of the fusion of the PPA polymer.
  • the PPA polymers of interest herein have a heat of fusion of no more than 50 Joules per gram ("J/g"). In some embodiments, the PPA polymers have a heat of fusion of no more than 45 J/g or no more than 40 J/g. The heat of fusion can be measured as described in the examples. Still further, the PPA polymers have a selected thermal window, defined by the difference between T d and T m (T d -T m ), of at least 60° C. In some embodiments, the PPA polymers have a thermal windows of no more than 200° C or no more than 120° C. Td and Tm can be measured as described in the examples below.
  • the concentration of the at least one semi-crystalline PPA polymer in the polymer matrix is at least 50 wt.%, at least 60 wt.%, at least 70 wt.% at least 80 wt.%, at least 90 wt.%, at least 95 wt.% or at least 99.5 wt.%, relative to the total weight of the matrix composition.
  • the at least one semi-crystalline PPA polymer of the polymer matrix can include a plurality of distinct semi-crystalline PPA polymers.
  • the total concentration of the semi-crystalline PPA polymers is within the ranges described above.
  • the polymer matrix in addition to the at least one semi-crystalline PPA polymer, can further include optional additives, including but not limited to, antioxidants (e.g. ultraviolet light stabilizers and heat stabilizers), processing aids, nucleating agents, lubricants, flame retardants, a smoke-suppressing agents, anti-static agents, anti-blocking agents, and conductivity additives such as carbon black.
  • antioxidants e.g. ultraviolet light stabilizers and heat stabilizers
  • processing aids e.g. ultraviolet light stabilizers and heat stabilizers
  • nucleating agents e.g. ultraviolet light stabilizers and heat stabilizers
  • lubricants e.g., flame retardants
  • a smoke-suppressing agents e.g. ultraviolet light stabilizers and heat stabilizers
  • anti-static agents e.g., anti-static agents, anti-blocking agents
  • conductivity additives such as carbon black.
  • antioxidants can be particularly desirable additives.
  • Antioxidants can improve the heat and light stability of the polymer matrix in the composite.
  • antioxidants that are heat stabilizers can improve the thermal stability of the composite during manufacturing (or in high heat application settings), for example, by making the polymer processable at higher temperatures while helping to prevent polymer degradation.
  • the antioxidants that are light stabilizers can further prevent against polymer degradation during use of the composite application settings where it is exposed to light (e.g. external automobile or aircraft parts).
  • Desirable antioxidants include, but are not limited to, copper salts (e.g. CuO and Cu 2 O), alkaline metal halides (e.g.
  • CuI, KI, and KBr including combinations of alkaline metal halides such as, but not limited to, CuI/KI), hindered phenols, hindered amine light stabilizers ("HALS”) (e.g. tertiary amine light stabilizers) and organic or inorganic phosphorous-containing stabilizers (e.g. sodium hypophosphite or manganese hypophosphite).
  • alkaline metal halides such as, but not limited to, CuI/KI
  • hindered phenols such as, but not limited to, CuI/KI
  • HALS hindered amine light stabilizers
  • organic or inorganic phosphorous-containing stabilizers e.g. sodium hypophosphite or manganese hypophosphite.
  • the total concentration of additives in the polymer matrix is 0 wt.%, at least 0.1 wt.%, at least 0.2 wt.%, at least 0.3 wt.%, or at least 0.4 wt.%, relative to the total weight of the polymer matrix. Additionally or alternatively, the total concentration of additives in the polymer matrix is no more than 10 wt.%, no more than 8 wt.%, no more than 6 wt.%, no more than 5 wt.%, no more than 4 wt.%, no more than 3 wt.%, no more than 2 wt.% or no more than 1 wt.%, relative to the total weight of the polymer matrix.
  • the thermoplastic composite includes at least one continuous reinforcing fiber.
  • the at least one continuous reinforcing fiber is selected from glass fiber, carbon fibers, aluminum fiber, titanium fiber, magnesium fiber, boron carbide fibers, rock wool fiber, steel fiber, aramid fiber, natural fiber (e.g. cotton, linen and wood) and any combination of one or more, thereof.
  • the at least one continuous reinforcing fiber is glass fiber or carbon fiber.
  • the at least one reinforcing fiber is continuous reinforcing fibers, meaning they have an average length in the longest dimension of at least 5 millimeters ("mm"), at least 10 mm, at least 25 mm or at least 50 mm.
  • the thermoplastic composite includes at least 20 wt.%, at least 25 wt.%, at least 30 wt.%, at least 35 wt.%, at least 40 wt.%, at least 45 wt.%, at least 50 wt.% or at least 55 wt.% of the continuous reinforcing fiber, relative to the total weight of the thermoplastic composite. Additionally or alternatively, the thermoplastic composite includes no more than 80 wt.%, no more than 75 wt.%, no more than 70 wt.%, no more than 65 wt.% or no more than 60 wt.% of the continuous reinforcing fiber, relative to the total weight of the thermoplastic composite. In embodiments in which the at least one continuous reinforcing fiber is a plurality of continuous reinforcing fibers, the total concentration of continuous reinforcing fibers is within the ranges above.
  • the composites include the reinforcing fiber impregnated with the polymer matrix.
  • the composites can be unidirectional composites.
  • the composite can be a multidirectional composite, in which the fibers have a more complex structure.
  • Fig. 1 is a schematic depiction showing a perspective view of an embodiment unidirectional composite.
  • tape 100 includes reinforcing fibers 102 and polymer matrix 104. Reinforcing fibers 102 are generally aligned along their length. Dashed lines 106 (not all labelled, for clarity) denote the orientation of continuous reinforcing fibers 102.
  • generally aligned fibers are oriented such that at least 70%, at least 80%, at least 90% or at least 95% of the reinforcing fibers have length that is within 30 degrees, within 25 degrees, within 20 degrees, within 15 degrees, or within 10 degrees along a length of one of the fibers.
  • the composite can be a multidirectional composite (e.g. laminate).
  • unidirectional composites have fibers that are generally aligned along a single direction. Because the tensile strength of the composite is greater along the length of the fiber, unidirectional composites have excellent tensile strength along a single dimension, and reduced tensile strength along other ( e.g. perpendicular) directions.
  • multidirectional composites have reinforcing fibers aligned along multiple dimensions and, therefore, have improved tensile strength in multiple dimensions ( e.g. more isotropic).
  • the reinforcing fibers in the polymer matrix can be arranged as a woven fabric or a layered fabric or any combination of one or more therefore.
  • Fig. 2 is a schematic depiction showing a perspective view of an embodiment of a multidirectional composite in which the reinforcing fibers are oriented as a woven fabric.
  • multidirectional composite 200 includes polymer matrix 206 and reinforcing fibers 202 and 204, which are generally perpendicular to each other. For clarity, not all reinforcing fibers are labelled in Fig. 2 .
  • each reinforcing fibers 202 and 204 can include bundle of reinforcing fibers.
  • reinforcing fibers 202 and 204 can be a yarn or layer (e.g. a planar distribution of single reinforcing fibers adjacent each other) of reinforcing fibers.
  • Fig. 3 is a schematic depiction showing a perspective view of an embodiment of a multidirectional composite in which the continuous reinforcing fibers are oriented as a layered fabric.
  • multidirectional composite 300 includes reinforcing fibers 302 and 304 and polymer matrix 306.
  • reinforcing fibers 302 and 304 are present in polymer matrix 306 as different layers, with the reinforcing fibers 302 generally aligned parallel with each other and reinforcing fibers 304 generally aligned parallel with each other.
  • Reinforcing fibers 302 are also generally aligned at an angle with reinforcing fibers 304.
  • Dashed lines 308 indicate the alignment of fiber 304 within the multidirectional composite 300.
  • Pluses (“+") 310 indicate the alignment of fibers 302 within multidirectional composite 300.
  • the angle between fibers 302 and 304 along their respective lengths is at least 15 degrees, at least 30 degrees or at least 40 degrees and no more than about 75 degrees, no more than about 60 degrees or no more than about 50 degrees.
  • the layered fabric can have additional layers of reinforcing fibers, aligned at the same angle or different angles as the reinforcing fibers in another layer in the multidirectional composite.
  • the composites can be fabricated by methods well known in the art.
  • composite fabrication includes impregnation of the reinforcing fibers with the polymer matrix material ("melt impregnation"), and subsequent cooling to room temperature (20° C to 25° C) form the final solid composite.
  • the melt impregnation includes contacting the reinforcing fibers with a melt of the polymer matrix material.
  • the melt is at a temperature of at least Tm* to less than Td*, where Tm* is the melt temperature of the PPA polymer in the polymer matrix having the highest melt temperature and Td* is the onset decomposition temperature of the PPA polymer having the lowest onset decomposition temperature in the melt.
  • melt impregnation can further include mechanical compression of the melt against the fibers.
  • the polymer matrix material is heated to form a melt and mechanically compressed against the fibers simultaneously.
  • the fibers can first be contacted with the melt and subsequently mechanically compressed.
  • the impregnated reinforcing fibers are cooled to form a solid composite.
  • the composite can be shaped to a desired geometry prior to be cooled to room temperature.
  • the impregnated reinforcing fibers can be passed through a die to form the composite having the desired geometry.
  • One example of a composite fabrication method includes pultrusion.
  • pultrusion a plurality of fibers are aligned along their length and pulled in a direction along their length.
  • the plurality of fibers is delivered from a spool(s) of the reinforcing fiber.
  • the fibers are pulled through a bath including a melt of the polymer matrix. After being pulled through the melt, in some embodiments, the impregnated fibers can be further heated to further aid in the impregnation. Additionally or alternatively, the impregnated fibers can be pulled through a die and to provide the desired shape to the composite, prior to cooling to room temperature. Pultrusion can be particularly desirable in the formation of unidirectional composites.
  • a composite fabrication method includes a slurry process.
  • a slurry process a slurry is formed by adding the polymer matrix, in powdered form, to a liquid medium to create a suspension.
  • the slurry is coated onto a surface of the fibers, for example, by passing the fibers through a bath of the slurry. Subsequently, the coated fibers are then heated and consolidated (e.g. by heated mechanical rollers). Slurry fabrication can be desirable for the formation of composite tapes.
  • Yet another example of a composite fabrication method involves direct powder deposition. In such a method, the polymer matrix, in powder form, is deposited onto the surface of the fibers and subsequently heated to melt the polymer matrix. Direct powder deposition can be desirable to form woven fabric compositions.
  • composited can be formed by thermopressing of a two or more composites.
  • two or more composites can be thermo-pressed (e.g. heated and mechanically pressed together) to form a new composite.
  • composite 300 can be formed by thermopressing two unidirectional composites (e.g. composite 100), oriented such the reinforcing fibers of each composite are at the desired angle to one another.
  • one or more composites according to composite 200 can be pressed together to form another composite.
  • each composite prior to thermopressing, each composite can be oriented to achieve the desired relative fiber alignment between each of the composites being thermopressed.
  • the composite can be overmolded with another polymer composition.
  • a polymer composition including reinforcing fibers can be injection molded onto a portion of the composite.
  • the reinforcing fibers generally have a length of less than 5 mm.
  • a polymer composition including a polyamide and reinforcing glass or carbon fibers can be injection molded onto at least a portion of the thermoplastic composite.
  • the polyamide can be an amorphous or semi-crystalline polyamide, preferably a semi-crystalline polyamide.
  • thermoplastic composites described herein can be desirably incorporated into articles for use in a wide variety of application settings.
  • the thermoplastic composites can be integrated into automotive components including, but not limited to, pans (e.g. oil pans), panels (e.g. exterior body panels, including but not limited to quarter panels, trunk, hood; and interior body panels, including but not limited to, door panels and dash panels), side-panels, mirrors, bumpers, bars (e.g., torsion bars and sway bars), rods, suspensions components (e.g., suspension rods, leaf springs, suspension arms), and turbo charger components (e.g. housings, volutes, compressor wheels and impellers).
  • the thermoplastic composites described herein can also be desirably integrated into aerospace components, oil and gas drilling components (e.g. downhole drilling tubes, chemical injection tubes, undersea umbilicals and hydraulic control lines) and mobile electronic device components.

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